JPH04334339A - Aromatic compound, its production and noxious organism controlling agent containing the same as active ingredient - Google Patents

Abstract

PURPOSE:To obtain a new aromatic compound, having juvenile-like hormone activity against insects and capable of mainly acting as a growth regulator, a sterilizing agent, an ovicidal agent and a growth inhibitor on various insect pests including those having developed resistance to the existing insecticides and exhibiting high noxious organism controlling effects. CONSTITUTION:An aromatic compound expressed by formula I(R<1> is H, Cl or F; R<2> is H or methyl; R<3> is methyl, ethyl, Cl or Br), e.g. 4-benzyl-2-chloro-1-(4- ethylbenzyloxy)benzene. The aforementioned compound is obtained by reacting a compound expressed by formula II (M is H or alkali metal) with a compound expressed by formula III (A is halogen) or reacting a compound expressed by formula IV with a compound expressed by formula V. Furthermore, the above-mentioned compound has excellent controlling effects on insect pests of the orders Hemiptera, Lepidoptera, Diptera, Coleoptera, Dictyoptera, Thyseanoptera, Orthoptera, Hymenoptera, Anoplura, Siphonaptera, Homoptera, etc., especially the insect pests of the order Hemiptera, above all leafhoppers and planthoppers.

Description

[Detailed description of the invention]

0001

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel aromatic compound, a method for producing the same, and a pest control agent containing the aromatic compound as an active ingredient.

0002

[Prior Art] Until now, it has been reported that certain aromatic compounds have a pest control effect, for example, in
It is described in Publication No. 2235.

0003

[Problems to be Solved by the Invention] However, these compounds cannot always be said to be sufficient as effective ingredients for pest control agents.

0004

[Means for Solving the Problems] In view of the above-mentioned circumstances, the present inventors have conducted intensive studies to find a compound having a better pest control effect, and have developed the following general formula.
The present invention was completed based on the discovery that the aromatic compound represented by Chemical Formula 6 (hereinafter referred to as the compound of the present invention) has extremely high juvenile hormone-like activity. That is, the present invention provides general formula 6

[0005]

[C6]

[In the formula, R1 represents a hydrogen atom, a chlorine atom or a fluorine atom, R2 represents a hydrogen atom or a methyl group, and R3 represents a methyl group, an ethyl group, a chlorine atom or a bromine atom. The present invention provides an aromatic compound represented by the following, a method for producing the same, and a pest control agent containing the aromatic compound as an active ingredient.

The compounds of the present invention are markedly different from most conventional insecticides in that they have excellent juvenile hormone-like activity against insects. That is, it exhibits effects such as inhibiting metamorphosis into adult worms, inhibiting egg hatching, and sterilizing adult worms. As a result, the compounds of the present invention can be used against various pests, including pests that have developed resistance to existing insecticides, such as agricultural, forestry, and horticultural pests.
It mainly acts as a growth regulator, sterilizing agent, ovicidal agent, or growth inhibitor against grain storage pests, satellite pests, etc., and exhibits a high control effect.

The compound of the present invention represented by the general formula 6 can be produced, for example, by the following method.

(Production method A) General formula: Chemical formula 7

0010

[C7]

[In the formula, M represents an alkali metal atom or a hydrogen atom, and R1 represents the same meaning as above. ] and the general formula 8

0012

[Chemical formula 8]

[In the formula, A represents a halogen atom, and R2
and R3 have the same meanings as above. ] It can be produced by reacting with the compound shown below.

Examples of the base used include caustic alkalis such as caustic potash and caustic soda, alkali carbonates such as potassium carbonate and sodium carbonate, alkali metals such as sodium metal, hydrides of alkali metals such as sodium hydride, or sodium methoxide. , sodium ethoxide, triethylamine, pyridine, and other organic bases. Further, if necessary, a catalyst such as an ammonium salt (for example, triethylbenzylammonium chloride, etc.) may be added to the reaction system.

The reaction temperature can range from -20°C to the boiling point of the solvent used in the reaction, but -5°C
It is more desirable that the range is from to the boiling point of the solvent used in the reaction.

Although the molar ratio of the raw materials and base to be subjected to the reaction can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it.

The above reaction is preferably carried out in an inert solvent in the presence of a suitable base. However, when M is an alkali metal atom, the presence of a base is not necessarily required.

Examples of the solvent used include lower alcohols such as ethanol, propanol, isopropanol, and tertiary butyl alcohol, ketones such as acetone and methyl ethyl ketone, hydrocarbons such as benzene and toluene, diethyl ether, diisopropyl ether, Ethers such as tetrahydrofuran and dioxane, N,N
Examples include amides such as dimethylformamide and hexamethylphosphoric triamide, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene, dimethyl sulfoxide, acetonitrile, nitromethane and water. A mixed solvent of these solvents can also be used if necessary.

After completion of the reaction, the reaction solution can be subjected to conventional post-treatments such as organic solvent extraction and concentration to obtain the desired compound of the present invention. If necessary, it can be purified by conventional operations such as chromatography, distillation, recrystallization, etc.

(Production method B) General formula: Chemical formula 9

[0021]

[Chemical formula 9]

[In the formula, R1] has the same meaning as above. ] Phenolic compounds represented by the general formula Chemical formula 10

[
0023

[Chemical formula 10]

[In the formula, R2 and R3 have the same meanings as above. ] It can be produced by reacting with an alcoholic compound shown in the following.

The above reaction is particularly advantageous when R2 is not a hydrogen atom, and the reaction is preferably carried out in the presence of a suitable dehydrating catalyst or dehydrating agent, if necessary, in an inert solvent.

Examples of the dehydration catalyst used include inorganic acids such as hydrochloric acid and sulfuric acid, aromatic sulfonic acids and sulfonic acid chloride, and examples of the dehydration agent include dicyclohexylcarbodiimide, diisopropylazodicarboxylate, and the like. Examples include diethyl azodicarboxylate.

Examples of the solvent used include hydrocarbons such as benzene, toluene and xylene, and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane and chlorobenzene.

The reaction temperature can range from -20°C to 200°C or the boiling point used.

Although the molar ratio of the raw materials and dehydrating agent to be subjected to the reaction can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it.

After completion of the reaction, the reaction solution can be subjected to conventional post-treatments such as organic solvent extraction and concentration to obtain the desired compound of the present invention. If necessary, it can be purified by conventional operations such as chromatography, distillation, recrystallization, etc.

[0031] Among the compounds of the present invention, in the case of compounds having an asymmetric carbon atom, the compounds of the present invention can be used in their respective optically active isomers ((+)-isomer, (-)-isomer) and their respective optically active isomers ((+)-isomer, (-)-isomer). It also includes mixtures of in all proportions.

General formula (7) as a raw material for the compound of the present invention
Among the phenolic compounds represented by the above, the phenolic compound in which M represents an alkali metal atom can be derived and synthesized from the phenolic compound represented by the general formula (9). Further, the phenolic compound represented by the general formula 7 or the general formula 9 is described, for example, in J. Amer.
Chem. Soc. , 73, 2723 (1951),
J. Org. Chem. , 39, 1160 (1974)
It can be synthesized according to the method described in et al. That is, the general formula

[0033]

[Chemical formula 11]

[In the formula, R1 represents the same meaning as above. The phenol compound represented by formula 9 can be synthesized by reacting the phenol compound represented by formula 9 with a chlorinating agent in the presence of a solvent.

In the above reaction formula, chlorine, t-butyl hypochlorite, sulfuryl chloride, etc. can be used as the chlorinating agent. Further, a solvent can be used if necessary, and examples of the solvent that can be used include dichloromethane, dichloroethane, carbon tetrachloride, benzene, acetic acid, and the like. It goes without saying that the solvent used here is selected depending on the type of chlorinating agent. The reaction temperature is
The range can be from -78°C to the boiling point of the solvent or chlorinating agent (sulfuryl chloride, etc.) used in the reaction, but -
The range is preferably from 20°C to the boiling point of the solvent or chlorinating agent (such as sulfuryl chloride) used in the reaction. Although the molar ratio of the raw materials and chlorinating agent to be subjected to the reaction can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it. After the reaction is complete, the reaction solution is extracted with an organic solvent,
The desired compound can be obtained by performing usual post-treatments such as concentration. If necessary, it can be purified by conventional operations such as chromatography, distillation, recrystallization, etc. The phenolic compound represented by the general formula 11, which is a raw material for the compound of the present invention, is described in J. Sci. Fd Agri
c. , 18, 325 (1967).

Furthermore, the general formula serving as a raw material for the compound of the present invention
The compound represented by Chemical Formula 8 or General Formula 10 is known and can be easily synthesized by using a commercially available compound or by a conventional method from a commercially available compound.

Next, Tables 1 and 2 show compounds of the present invention that can be produced according to these production methods.

[0038]

[Table 1]

[0039]

[Table 2]

[0040] Examples of pests against which the compounds of the present invention are effective include the following.

Hemiptera pests: Planthoppers such as the brown planthopper, white-backed planthopper, and brown planthopper, leafhoppers such as the black-spotted leafhopper, black-spotted leafhopper, black-spotted leafhopper, brown leafhopper, brown leafhopper, black-and-white leafhopper, cotton aphid, green peach aphid, etc. Aphids, stink bugs, whiteflies such as tobacco whitefly, and whitefly, scale insects, ground beetles, psyllids, etc.

[0042] Lepidopteran insect pests, such as the Japanese armyworm moth (Nikamei moth), the brown borer moth, and the Japanese armyworm moth, the armyworms, such as the fall armyworm, the fall armyworm, and the armyworm moth, the white butterflies, such as the white cabbage butterfly, the yellow leaf moths, such as the white leaf moth, the silver leaf moth, the leafminer moth, and the Japanese leafminer moth. , Pests of the genus Agrotis (A
grothis spp. ), Heliotis spp. (
Heliothis spp. ), diamondback moth, burr moth, carp moth, etc.

[0043] Diptera pests Culex mosquitoes such as Culex mosquitoes and Culex pipiens; Aedes mosquitoes such as Aedes aegypti and Aedes albopictus; Anopheles mosquitoes such as Anopheles chinensis; Chironomid mosquitoes; house flies such as house flies and giant house flies; Hana flies such as onion flies, fruit flies, fruit flies, fruit flies, fruit flies,
Butterflies, horseflies, blackflies, stable flies, etc.

004
4] Coleoptera Pests Corn rootworms such as Western corn rootworm and Southern corn rootworm, scarab beetles such as the Japanese corn rootworm and Japanese corn rootworm, weevils such as the brown weevil, rice water weevil, and bean weevil, and mealworms such as the brown rice beetle and the brown corn rootworm spp., potato beetles such as the yellow flea beetle and cucumber beetles, leaf beetles, Epilachna spp.

[0045] Pests of the order Ophthalmoptera include the German cockroach, the black cockroach, the American cockroach, the brown cockroach, the Japanese cockroach, etc.

[0046] Synopteran pests such as southern yellow thrips, brown thrips, and red thrips.

Hymenoptera pests Ants, sawflies such as sawflies, etc.

Orthoptera pests Mole crickets, grasshoppers, etc.

[0049] Cryptopteran pests Human flea etc.

[0050] Pests of the order Liceformes Human lice, pubic lice, etc.

[0051] It is effective against isopteran pests such as the Japanese termite and the domestic termite. Furthermore, among these, it is more suitable for controlling Hemiptera pests, and is particularly effective against planthoppers and leafhoppers that damage rice crops, and exhibits an excellent control effect.

[0052] By adding other insecticides and/or acaricides, the compound of the present invention can be practically applied to control pests in a wider variety of pests and in a more diverse range of usage situations. Suitable additives include, for example, fenitrothion [O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate], fenthion [
O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl]phosphorothioate], diazinon [2-isopropyl-4-methylpyrimidyl-6)-diethylphosphorothioate], chlorpyrifos [O,O
-diethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate], acephate [O,S-dimethyl-acetophosphoramide thioate], methidathion [S-2,3-dihydro-5-methoxy-2- Oxo-
1,3,4-thiadiazol-3-ylmethyl O,O-
dimethyl phosphorodithioate], ethyl thiometone [
O,O-diethyl S-2-ethylthioethyl phosphorodithioate], DDVP [2,2-dichlorovinyl dimethyl phosphate], sulprophos [O-ethyl
O-4-(methylthio)phenyl S-propyl phosphorodithioate], dianophos [O-4-cyanophenyl O,O-dimethylphosphorothioate], salithion [2-methoxy-4H-1,3,2-benzodioxa] phosphorine-2-sulfide], dimethoate (
O,O-dimethyl-S-(N-methylcarbamoylmethyl)dithiophosphate], phenthoate [ethyl
2-dimethoxyphosphinothioylthio(phenyl)
acetate], malathion [diethyl(dimethoxyphosphinothioylthio)succinate], trichlorfone [dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate], azinphosmethyl [S-3,
4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O,O-dimethylphosphorodithioate], monocrotophos [dimethyl(E)-1-
Organophosphorus compounds such as methyl-2-(methylcarbamoyl)vinyl phosphate],

BPMC [2-sec-butylphenylmethyl carbamate], benfuracarb [ethyl N
-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-
N-isopropyl-β-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-2,2
-dimethyl-7-benzo[b]furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl[1-naphthyl-N-methylcarbamate], methomyl[S-methyl-N-[(methylcarbamoyl)oxy]
Thioacetimidate], Ethiophenecarb [2-(
ethylthiomethyl) phenylmethylcarbamate], aldicarb [2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyloxy], oxamyl [N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide ] and other carbamate compounds,

Ethofenprox [2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether], fenvalerate [(RS)-α-
Cyano-3-phenoxybenzyl (RS)-2-(4-
chlorophenyl)-3-methylbutyrate], esfanvalerate [(S)-α-cyano-3-phenoxybenzyl(S)-2-(4-chlorophenyl)-3-methylbutyrate], fenpropathrin [ (RS)-α-
Cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], Cypermethrin [(RS)-α-cyano-3-phenoxybenzyl (1RS,3RS)-(1RS,3RS)-3 −(2
, 2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl(1RS,3RS)-(1RS,3RS)-
3-(2,2-dichlorovinyl)-2,2-methylcyclopropanecarboxylate], cyhalothrin [(RS
)-α-cyano-3-phenoxybenzyl (Z)-(1
RS,3RS)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S)-α-
Cyano-m-phenoxybenzyl 1R,3R)-3(2
, 2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate], cycloprothrin [(RS)
-α-cyano-3-phenoxybenzyl (RS)-2,
pyrethroid compounds such as 2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate],

Buprofezin (2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-
thiadiazine derivatives such as triadiazinan-4-one), nitroimidazolidine derivatives such as imidacloprid (1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine), cartap (
S,S'-(2-dimethylaminotrimethylene)bis(
thiocarbamate)], thiocyclam [N,N-dimethyl-1,2,3-trithian-5-ylamine], bensultap [S,S-2-dimethylaminotrimethylene di(benzene thiosulfonate)], etc. Lystoxin derivative, endosulfan [6,7,8,9,10
,10-hexachloro-1,5,5a,6,9,9a-
hexahydro-6,9-methano-2,4,3-benzodioxathiepine oxide], γ-BHC[1,2,3
, 4,5,6-hexachlorocyclohexane], chlorfluavron [1-[3,
5-dichloro-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl]-3-(2
, 6-difluorobenzoyl)urea], teflubenzuron [1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea], flufenoxuron [1-[4- (2-chloro-
Benzoylphenylurea compounds such as 4-trifluoromethylphenoxy)-2-fluorophenyl-3-(2,6-difluorobenzoyl)urea], amitraz[N,N'[(methylimino)dimethylidine]di-2
, 4-xylidine], chlordimeform [N'-(4-
Examples include formamidine derivatives such as chloro-2-methylphenyl-N,N-dimethylmetanimidamide].

When the compound of the present invention is used as an active ingredient of a pest control agent, it may be used as it is without adding any of the ingredients described above, but it is usually used in combination with a solid carrier, liquid carrier, gaseous carrier, or bait. If necessary, surfactants and other formulation auxiliaries are added to produce flowable agents such as oils, emulsions, wettable powders, suspensions and emulsions in water, granules, powders, etc.
It is used in formulations such as aerosols, heating smokers such as self-combustion type smokers, chemical reaction type smokers, and porous ceramic plate smokers, ULV agents, and poison baits.

These preparations usually contain the compound of the present invention as an active ingredient in an amount of 0.001% to 95% by weight. Solid carriers used in formulation include, for example, clays (kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (sericite, quartz,
Sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphorus, ammonium nitrate, urea, ammonium chloride, etc.), and other fine powders or granules.As liquid carriers, for example, water, alcohol, etc. (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.) ), esters (
ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N
-dimethylformamide, N,N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, vegetable oils such as soybean oil, cottonseed oil, etc.; Examples of the agent include chlorofluorocarbon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether,
Examples include carbon dioxide gas.

Examples of surfactants include alkyl sulfate esters, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers and their polyoxyethylenic products, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohols. Examples include derivatives.

Examples of formulation auxiliaries such as fixing agents and dispersants include casein, gelatin, polysaccharides (starch powder,
Gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), etc. Stabilizers include PAP (acidic phosphoric acid, etc.). isopropyl), BHT (2,
6-di-tert-butyl-4-methylphenol),
Examples include BHT (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, surfactant, fatty acid or its ester, and the like.

Examples of base materials for self-combusting smoke agents include nitrates, nitrites, guanidine salts, potassium chlorate,
Combustion exothermic agents such as nitrocellulose, ethyl cellulose, and wood flour; thermal decomposition stimulators such as alkali metal salts, alkaline earth metal salts, dichromates, and chromates; oxygen supply agents such as potassium nitrate; melamine and wheat starch. Examples include combustion supporting agents such as, fillers such as diatomaceous earth, binders such as synthetic glues, etc. Examples of base materials for chemically reactive smoke agents include alkali metal sulfides, polysulfides, hydrosulfides, hydrated salts,
Exothermic agents such as calcium oxide, carbonaceous substances, iron carbide, catalyst agents such as activated clay, organic blowing agents such as azodicarbonamide, benzenesulfonyl hydrazide, dinitrosopentamethylenetetramine, polystyrene, polyurethane, natural fiber pieces, synthetic fibers Examples include fillers such as pieces.

Poisonous bait base materials include, for example, grain flour, vegetable essential oil, sugar, bait components such as crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, and chili pepper. Examples include agents to prevent accidental ingestion of powder, etc., and attractive flavorings such as cheese flavoring and onion flavoring.

The formulation of flowables (suspensions or emulsions in water) generally contains 1 to 75% of the compound in a proportion of 0.5 to 1
5% dispersant, 0.1-10% suspension aid (e.g.
compounds that impart protective colloids and thixotropic properties),
In water containing 0 to 1.0% of suitable adjuvants (e.g. antifoaming agents, rust inhibitors, stabilizers, spreading agents, penetration aids, antifreeze agents, antibacterial agents, antismoke agents, etc.) It can be obtained by finely dispersing it. It is also possible to use an oil in which the compound hardly dissolves in place of water to form a suspension in oil. As the protective colloid, for example, gelatin, casein, gums, cellulose ether, polyvinyl alcohol, etc. are used. Examples of compounds that impart thixotropy include bentonite, aluminum magnesium silicate, xanthan gum, and polyacrylic acid.

The preparation thus obtained can be used as it is or diluted with water or the like. Also, other insecticides,
It can also be used simultaneously with or without mixing with nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feed, etc.

When the compound of the present invention is used as an agricultural pest control agent, the application amount is usually 0.001 g to 500 g per 10 ares, preferably 0.001 g to 500 g per 10 ares.
The amount is from 1g to 500g. When using emulsions, wettable powders, flowables, etc. diluted with water, the application concentration is usually
It is 0.0001 ppm to 1000 ppm, and granules, powders, etc. are applied as they are without any dilution. In addition, when used as a pest control agent for epidemic prevention,
Emulsions, wettable powders, flowables, etc. are usually 0.000% in water.
Apply diluted to 1 ppm to 10,000 ppm, and apply as is for oils, aerosols, smoke agents, ULV agents, poison baits, etc.

[0065] These application amounts and application concentrations vary depending on the type of preparation, application time, application location, application method, type of pest, degree of damage, etc., and may be increased or increased without regard to the above range. It can be reduced.

[0066]

EXAMPLES The present invention will be explained in more detail below with reference to production examples, formulation examples, and test examples, but the present invention is not limited to these examples. First, a production example of the compound of the present invention will be shown.

Production Example 1 (Production method for compound (1)) 0.265 g of potassium carbonate, 0.4 g of 4-benzyl-2-chlorophenol, 0.4 g of p-methylbenzyl chloride.
275 g and anhydrous N,N-dimethylformamide 1
The 5 ml mixture was stirred at room temperature overnight. After the reaction solution was poured into ice water, it was extracted twice with 100 ml of diethyl ether. The ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography, and 4-benzyl-2-chloro-1-(4-methylbenzyloxy)benzene 0.47
I got g. Yield: 81% n23.1D: 1.6032

Production Example 2 (Production method of compound (2)) 4-benzyl-2-
Chlorophenol 0.81g, p-ethylbenzyl alcohol 0.50g, triphenylphosphine 1.00g
A mixture of 0.65 g of diethyl azodicarboxylate and 20 ml of anhydrous tetrahydrofuran was stirred at room temperature for 48 hours. The reaction solution was concentrated, 50 ml of diethyl ether was added, and the precipitate was filtered. After concentrating the filtrate, it was subjected to silica gel chromatography to extract 4-benzyl-2-chloro-1-(4-ethylbenzyloxy)benzene.
74g was obtained. Yield: 59% n23.4D: 1.5971

Production Example 3 (Production method of compound (9)) 4-benzyl-2-
Chlorophenol 0.50g, 1-(4-chlorophenyl)ethanol 0.36g, triphenylphosphine 0
．． 60g, diethyl azodicarboxylate 0.40g
A mixture of 20 ml of anhydrous tetrahydrofuran and 20 ml of anhydrous tetrahydrofuran was stirred at room temperature for 48 hours. The reaction solution was concentrated, 50 ml of diethyl ether was added, and the precipitate was filtered. After concentrating the filtrate, it was subjected to silica gel chromatography to obtain 0.43 g of 4-benzyl-2-chloro-1-[1-(4-chlorophenyl)ethoxy]benzene. Yield: 52% n23.1D: 1.5987

Next, Table 3 shows some of the compounds of the present invention obtained according to these production methods.

[0071]

[Table 3]

Next, an example of intermediate production will be shown. Intermediate production example (4-(3,5-difluorobenzyl)-
2-Chlorophenol production method) 4-(3,5-difluorobenzyl)phenol 9.8
g was dissolved in 300 ml of carbon tetrachloride, and 4.85 g of t-butyl hypochlorite was slowly added dropwise while stirring vigorously at -10°C or lower. After the dropwise addition was completed, the mixture was stirred at room temperature. 5
After an hour, the reaction mixture was concentrated, 200 ml of ethyl acetate was added to the residue, and the mixture was washed with 5% aqueous sodium bicarbonate. After drying and concentrating the ethyl acetate solution, the residue was subjected to silica gel chromatography to obtain 4-(3,5-difluorobenzyl)-2-
9.68 g of chlorophenol was obtained. Yield: 85% m・p・: 40.9°C

The following formulation examples are shown below. In addition, parts represent parts by weight, and the compounds of the present invention are represented by the compound numbers listed in Table 3.

Formulation Example 1 Emulsion 10 parts each of the compounds (1) to (9) of the present invention were dissolved in 35 parts of xylene and 35 parts of dimethylformamide, and 14 parts of polyoxyethylene styryl phenyl ether was dissolved therein.
1 part and 6 parts of calcium dodecylbenzenesulfonate were added and mixed with thorough stirring to obtain each 10% emulsion.

Formulation Example 2 Wettable powder 20 parts each of the compounds (1) to (9) of the present invention were mixed with 4 parts of sodium lauryl sulfate and 2 parts of calcium ligninsulfonate.
1 part, 20 parts of synthetic hydrated silicon oxide fine powder, and 54 parts of diatomaceous earth were added to the mixture, and the mixture was stirred and mixed with a juice mixer to obtain each 20% hydrating powder.

Formulation Example 3 Granules 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 60 parts of clay are added to 5 parts each of the compounds (1) to (9) of the present invention, and the mixture is stirred and mixed thoroughly. Then,
An appropriate amount of water is added to these mixtures, which are further stirred, granulated using a granulator, and dried through ventilation to obtain each 5% granule.

Formulation Example 4 Powder 0.3 parts each of the compounds (1) to (9) of the present invention, 1 part of synthetic hydrated silicon oxide fine powder, 1 part of the trade name Driles B (manufactured by Sankyosha) as a coagulant, and Clay 7 After thoroughly mixing 7 parts in a mortar, stir and mix with a juice mixer. 90 parts of cut clay was added to the resulting mixture and mixed in a bag to obtain each powder.

Formulation Example 5 Powder 0.3 parts each of the compounds (1) to (9) of the present invention, 2 parts of fenitrothion as an organic phosphorus compound, 3 parts of synthetic hydrous silicon oxide fine powder, and the product name Driles B (as a flocculant) (manufactured by Sankyosha) and 3.7 parts of clay were thoroughly mixed in a mortar, and then stirred and mixed with a juice mixer. 90 parts of cut clay was added to the resulting mixture and mixed in a bag to obtain each powder.

Formulation Example 6 Powder 0.3 parts each of the compounds (1) to (9) of the present invention, 2 parts of BPMC (O-sec-butylphenyl N-methylcarbamate) as a carbamate compound, synthetic hydrated silicon oxide fine powder Part 3, as a flocculant (trade name: Drillless B)
(manufactured by Sankyo Co., Ltd.) and 3.7 parts of clay were thoroughly mixed in a mortar, and then stirred and mixed with a juice mixer. 90 parts of cut clay was added to the resulting mixture and mixed in a bag to obtain each powder.

Formulation Example 7 Flowable agent Compound of the present invention (
10 parts of each of 1) to (9), 6 parts of polyvinyl alcohol
40 parts of an aqueous solution containing 50% of the total amount, and stirred with a mixer to obtain a dispersant. To this was added 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate, and 1 part of propylene glycol.
0 part was added and mixed with gentle stirring to obtain each 10% emulsion in water.

Formulation Example 8 Oil Agent 0.1 part of each of the compounds (1) to (9) of the present invention was dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this was mixed with 89.9 parts of deodorized kerosene. .1% oil solution is obtained.

Formulation Example 9 Oil aerosol 0.1 part each of the compounds (1) to (9) of the present invention, 0.2 parts of tetramethrin
parts, 0.1 parts of d-phenothrin, 10 parts of trichloroethane
After mixing and dissolving 59.6 parts of deodorized kerosene and filling it into an aerosol container and attaching a bubble part, 30 parts of a propellant (liquefied petroleum gas) was pressurized and filled through the valve part to make each oil-based aerosol. obtain.

Formulation Example 10 Aqueous aerosol 0.2 parts each of the compounds (1) to (9) of the present invention, 0.2 parts of d-allethrin.
2 parts of d-phenothrin, 0.2 parts of xylene, 3.4 parts of deodorized kerosene, and 1 part of emulsifier {Atmos 300 (registered trademark of Atlas Chemical Co., Ltd.)} were mixed and dissolved;
An aerosol container is filled with 50 parts of pure water, a valve part is attached, and 40 parts of a propellant (liquefied petroleum gas) is pressurized and filled through the valve part to obtain each aqueous aerosol.

Formulation Example 11 Heat-smoking agent Compound of the present invention (
100 mg of each of 1) to (9) was dissolved in an appropriate amount of acetone and impregnated into a porous ceramic plate of 4.0 cm x 4.0 cm and 1.2 cm thick to obtain each hot smoking agent.

Next, it will be shown by test examples that the compounds of the present invention are useful as active ingredients of pest control agents. The compounds of the present invention are indicated by the compound numbers listed in Tables 1 and 2, and the compounds used for comparison are indicated by the compound numbers listed in Table 4.

[0086]

[Table 4]

Test Example 1 Metamorphosis inhibitory effect on brown planthopper larvae An emulsion of the test compound obtained according to Preparation Example 1 was diluted with water to a predetermined concentration and applied to rice seedlings planted in polyethylene cups in 20ml/2 pots. It was distributed in proportion. After air drying, 10 brown planthopper 3rd instar larvae were released per pot.
After several days, the inhibition rate of emergence was determined. The results are shown in Table 5.

[0088]

[Table 5]

Compounds of the present invention (1) and (2) inhibited eclosion by 100% at a test concentration of 5 ppb, and compounds of the present invention (4) and (5) at a test concentration of 0.5 ppm.

[0090]

[Effects of the Invention] The compounds of the present invention are effective against Hemiptera pests, Lepidoptera pests, Diptera pests, Coleoptera pests, Reciptate pests, Thymoptera pests, Orthoptera pests, Hymenoptera pests, and cryptopteran pests. It has an excellent control effect against insect pests of the Order order, Prunus order, pests of the order Isoptera, etc., and can be used for various purposes as a harmful control agent.

Claims (4)

[Claims] Claim 1: General formula: Chemical formula 1: [In the formula, R1 represents a hydrogen atom, a chlorine atom or a fluorine atom, R2 represents a hydrogen atom or a methyl group, and R3
represents a methyl group, ethyl group, chlorine atom or bromine atom. ] Aromatic compounds represented by Claim 2: General Formula 2 [In the formula, R1 represents a hydrogen atom, a chlorine atom or a fluorine atom, and M represents a hydrogen atom or an alkali metal atom. [In the formula, R2 represents a hydrogen atom or a methyl group, and R3
represents a methyl group, an ethyl group, a chlorine atom or a bromine atom, and A represents a halogen atom. 2. The method for producing an aromatic compound according to claim 1, wherein the aromatic compound is reacted with a compound represented by the following. Claim 3: General Formula 4 [In the formula, R1 represents a hydrogen atom, a chlorine atom or a fluorine atom]. ] Phenolic compounds and general formula
Chemical formula 5 [Chemical formula 5] [In the formula, R2 represents a hydrogen atom or a methyl group, and R3
represents a methyl group, ethyl group, chlorine atom or bromine atom. 2. The method for producing an aromatic compound according to claim 1, wherein the aromatic compound is reacted with an alcohol compound represented by the following. 4. A pest control agent containing the aromatic compound according to claim 1 as an active ingredient.